This invention relates to coatings for implantable ophthalmic lenses. In particular, the present invention relates to hydrophilic coatings that are applied to the edge of implantable ophthalmic lenses.
Both rigid and foldable implantable ophthalmic lens materials are known. The most common rigid material used in ophthalmic implants is polymethyl methacrylate (xe2x80x9cPMMAxe2x80x9d). Foldable intraocular lens (xe2x80x9cIOLxe2x80x9d) materials can generally be divided into three categories: silicone materials, hydrogel materials, and non-hydrogel (xe2x80x9chydrophobicxe2x80x9d) (meth)acrylic materials. See, for example, Foldable Intraocular Lenses, Ed. Martin et al., Slack Incorporated, Thorofare, N.J. (1993). For purposes of the present application, hydrophobic (meth)acrylic materials are (meth)acrylic materials that absorb less than approximately 5% water at room temperature.
As described in U.S. Pat. No. 5,755,786, IOLs, particularly IOLs designed for implantation through a small incision, can suffer from a problem of edge glare. The invention described in the ""786 patent reduces edge glare by including means, such as a plurality of v-shaped grooves, on the optic edge""s surface for reflecting visible light that contacts the edge surface away from the retina of the patient.
Other methods of reducing edge glare include those described in U.S. Pat. Nos. 5,693,093; 5,769,889; 4,808,181; and 4,605,409.
The present invention relates to hydrophilic coating compositions for surgical implants, particularly ophthalmic implants comprising silicone or hydrophobic (meth)acrylic materials. More specifically, the present invention relates to a coating material comprising an ophthalmically acceptable hydrophobic (meth)acrylic polymer and an ophthalmically acceptable hydrophilic polymer.
The present invention also relates to a method for reducing edge glare in implantable ophthalmic lenses. The method comprises applying a coating comprising an ophthalmically acceptable hydrophobic (meth)acrylic polymer and an ophthalmically acceptable hydrophilic polymer to an implant""s optic edge surface. When hydrated, the coating is hazy or opaque and reduces or eliminates edge glare.
Unless indicated otherwise, all amounts are expressed as %(w/w).
As used herein hydrophobic xe2x80x9c(meth)acrylic polymerxe2x80x9d means a hydrophobic methacrylic polymer, a hydrophobic acrylic polymer, or a hydrophobic copolymer containing both methacrylic and acrylic functional groups. As used herein, xe2x80x9chydrophobicxe2x80x9d means the materials absorb less than approximately 5% water at room temperature.
The coating material of the present invention comprises an ophthalmically acceptable hydrophobic (meth)acrylic polymer and a hydrophilic polymer. When hydrated, the coating material has a Tg less than 37xc2x0 C., and preferably less than 15xc2x0 C. The hydrophobic (meth)acrylic polymer ingredient in the coating material is preferably tacky to aid in attaching the coating material to the substrate. Many ophthalmically acceptable hydrophobic (meth)acrylic polymers are known, including those described in U.S. Pat. Nos. 5,290,892; 5,693,095; and 5,331,073, the entire contents of which are hereby incorporated by reference. Although aliphatic (meth)acrylate monomers can be used to form the hydrophobic (meth)acrylic polymer, the hydrophobic (meth)acrylate polymer preferably comprises at least one (meth)acrylic monomer that contains an aromatic group, such as those materials defined in U.S. Pat. No. 5,693,095: 
wherein:
X is H or CH3;
m is 0-6;
Y is nothing, O, S, or NR, wherein R is H, CH3, CnH2n+1 (n=1-10), iso-OC3H7, C6H5, or CH2C6H5; and
Ar is any aromatic ring which can be unsubstituted or substituted with CH3, C2H5, n-C3H7, iso-C3H7, OCH3, C6H11, Cl, Br, C6H5, or CH2C6H5.
Suitable hydrophobic (meth)acrylic polymers include copolymers of 2-phenylethyl methacrylate (2-PEMA) and 2-phenylethyl acrylate (2-PEA).
After selecting the (meth)acrylic monomer(s), the hydrophobic (meth)acrylic polymer is formed using an initiator (generally about 2% or less). Any type of polymerization initiator may be used, including thermal initiators and photoinitiators. A preferred initiator is the benzoylphosphine oxide initiator, 2,4,6-trimethyl-benzoyidiphenylophosphine oxide (xe2x80x9cTPOxe2x80x9d), which can be activated by blue light or UV irradiation. Suitable thermal initiators include the conventional peroxides t-butyl peroctoate and bis-azoisobutronitrile. Suitable UV initiators include benzoin methyl ether, DAROCUR 1173 (2-hydroxy-2-methyl-1-phenyl-1-propanone) and DAROCUR 4265 (1:1 mixture of 2-hydroxy-2-methyl-1-phenyl-1-propanone and diphenyl(2,4,6-trimethylbenzoyl)-phosphine oxide) UV initiators.
The hydrophobic (meth)acrylic polymer optionally contains one or more ingredients selected from the group consisting of UV absorbers that are copolymerizable with the other (meth)acrylic ingredients; blue-light blocking colorants that are copolymerizable with the other (meth)acrylic ingredients; and chain transfer agents to minimize cross-linking.
Ultraviolet absorbing chromophores can be any compound which absorbs light having a wavelength shorter than about 400 nm, but does not absorb any substantial amount of visible light. Suitable copolymerizable ultraviolet absorbing compounds are the substituted 2-hydroxybenzophenones disclosed in U.S. Pat. No. 4,304,895 and the 2-hydroxy-5-acryloxyphenyl-2H-benzotriazoles disclosed in U.S. Pat. No. 4,528,311. The most preferred ultraviolet absorbing compound is 2-(3xe2x80x2-methallyl-2xe2x80x2-hydroxy-5xe2x80x2-methyl phenyl)benzotriazole. Suitable polymerizable blue-light blocking chromophores include those disclosed in U.S. Pat. No. 5,470,932. If a blue-light activated polymerization initiator is chosen and a blue-light blocking colorant is added, the polymerization initiator identity or concentration may have to be adjusted to minimize any interference.
Chain transfer agents, if present, are typically added in an amount ranging from 0.01 to 0.4%. Many chain transfer agents are known in the art. Examples of suitable chain transfer agents include 1-dodecanethiol and 2-mercaptoethanol.
The hydrophilic polymer contained in the coating materials of the present invention may be any ophthalmically acceptable hydrophilic polymer. Suitable hydrophilic polymers include, but are not limited to polyhydroxyethyl methacrylate (polyHEMA); polyacrylamide; polyglyceryl methacrylate and polyvinyl pyrrolidone (PVP). The most preferred hydrophilic polymer is PVP. These hydrophilic polymers are commercially available or can be made using known methods and are preferably obtained in a purified form in order to minimize extractables upon implantation of the coated IOL.
The hydrophilic polymer preferably has a molecular weight (weight avg.) in the range of 2,500-100,000. It is important that the hydrophilic polymer""s molecular weight be great enough and be present in the hydrogel coating material in a sufficient amount to form hydrophilic domains capable of dispersing light. The hydrophilic polymer should not be too small, otherwise an appreciable amount of it may leach out of the coating after the coating is applied to the IOL. The hydrophilic polymer should not be too large, otherwise it may affect intraocular pressure in the event that some of the polymer leaches out of the coating. In the case of PVP, a molecular weight of 10,000 is preferred.
The coating material is formed by preparing an ophthalmically acceptable hydrophobic (meth)acrylic polymer, then purifying (if necessary or desired) the cured hydrophobic (meth)acrylic polymer via extraction in a suitable solvent, then dissolving the hydrophobic (meth)acrylic polymer and an ophthalmically acceptable hydrophilic polymer in a suitable solvent or mixture of solvents to form a coating solution. The proportion of hydrophobic (meth)acrylic polymer to hydrophilic polymer in the coating composition depends upon on the desired hydrated water content for the coating, the desired thickness of the coating, the chosen hydrophobic (meth)acrylic and hydrophilic materials, etc. Once the desired coating thickness and water content are chosen, the proportion of hydrophobic (meth)acrylic polymer to hydrophilic polymer can be determined by routine calculations and experimentation. In general, the desired water content of the hydrated coating will range from about 20-70% and the desired coating thickness will range from 0.5-1 xcexcm. Typical concentrations of hydrophilic polymer in the coating material will therefore range from about 5 to about 50%, preferably from about 15 to about 30%.
The solvent or solvent mixture used to form the coating solution should be chosen to give a homogeneous coating solution. Because the coatings will be used to reduce glare, it is not necessary for the coating solution to be clear. Whether or not the coating solution is clear, the coating should be translucent to opaque after being applied to the implant""s edge and hydrated. An example of a suitable solvent mixture in the case of a 2-PEMA/2-PEA copolymer as the hydrophobic (meth)acrylic polymer and PVP as the hydrophilic polymer is a 2-pentanone/methanol mixture. In general, polar solvents such as alcohols will be suitable when the hydrophilic polymer is polyHEMA or polyglycerylmethacrylate, and ketones, such as 2-pentanone, or methyiene chloride, will be suitable when the hydrophilic polymer is polyacrylamide or PVP.
The coating material is preferably attached to the substrate IOL by means of one or both of the following: (1) hydrophobic or xe2x80x9cphysicalxe2x80x9d (i.e., non-covalent) cross-linking and (2) interpenetrating polymer networking. The coating material is intemally cross-linked by non-covalent cross-linking. Alternatively, the coating material may be covalently cross-linked to the IOL by means of a cross-linking agent.
The coating solution is applied to the implant""s edge surface by conventional techniques, such as spin- or dip-coating processes or casting a coating layer around a pre-formed rod of the optic material. Dip-coating is preferred. The implant is preferably dipped at such a rate so as to minimize any swelling of the implant caused by the solvent in the coating solution.
After the coating is applied to the implant, the coating is dried. A two-stage drying process is preferred. First, the coated implant is allowed to dry in air until most or all of the solvent has evaporated (generallyxe2x89xa615 minutes). Second, the coated implant is baked at elevated temperature, about 40-100xc2x0 C., to eliminate as much of the remaining solvent as possible. A preferred drying process involves room temperature air drying for 15 minutes, followed by baking at 90xc2x0 C. for about 20-60 minutes. If a covalent cross-linking agent is added to the coating solution, the coating is dried in a way that fully activates the cross-linking agent.
The coating can be easily removed by a variety of organic solvents or solvent mixtures, including the same solvent used as the base in the preparation of the coating solution. The coating cannot be removed by water, however.
The implants suitable for coating with the hydrophilic coatings of the present invention are preferably made of hydrophobic (meth)acrylic materials, but could also be constructed of silicone or silicone-(meth)acrylic copolymers. Preferred hydrophobic (meth)acrylic materials are those polymeric materials described in U.S. Pat. Nos. 5,290,892 and 5,693,095, the entire contents of which are hereby incorporated by reference. In the case where the implant is an IOL, the coatings of the present invention may be used in conjunction with substrate materials intended for use as a xe2x80x9chardxe2x80x9d IOL (that is inserted in an unfolded state) or a xe2x80x9cfoldablexe2x80x9d or xe2x80x9csoftxe2x80x9d IOL (that is inserted in a folded or compressed state). Suitable IOL materials to be coated include those disclosed in U.S. Pat. Nos. 5,693,095 or 5,331,073. As used herein, xe2x80x9cimplantsxe2x80x9d includes contact lenses.
When covalent cross-linking agents are used, it may be necessary or desirable to prepare the implant""s surface that will receive the coating by exposing the implant""s surface to a reactive plasma gas prior to applying the coating solution. Suitable reactive plasma gases include oxidizing gases, such as oxygen gas. A suitable plasma chamber is the P2CIM B-Series plasma chamber made by Advanced Plasma Systems, Inc. Using such a chamber, suitable plasma parameters include: power=400 W, plasma gas=oxygen; pressure of the plasma gas=225 mTorr; exposure time=4-6 minutes.
The following examples are intended to be illustrative but not limiting.